New Fusarochromanone Derivatives from the Marine Fungus Fusarium equiseti UBOCC-A-117302

Mar Drugs. 2024 Sep 28;22(10):444. doi: 10.3390/md22100444.

Abstract

Two new fusarochromanone derivatives, deacetylfusarochromene (1) and deacetamidofusarochrom-2',3-diene (2), along with the previously reported metabolites fusarochromanone TDP-2 (3), fusarochromene (4), 2,2-dimethyl-5-amino-6-(2'E-ene-4'-hydroxylbutyryl)-4-chromone (5), fusarochromanone (6), (-)-chrysogine (7), and equisetin (8), were isolated from the marine fungus Fusarium equiseti UBOCC-A-117302. The structures of the compounds were determined by extensive spectrometric (HRMS) and spectroscopic (1D and 2D NMR) analyses, as well as specific rotation. Among them, 2 and 5 showed inhibition of three protein kinases with IC50 values ranging from 1.42 to 25.48 μM. Cytotoxicity and antimicrobial activity of all isolated compounds were also evaluated. Six fusarochromanone derivatives (1-6) exhibited diverse activities against three cell lines, RPE-1, HCT-116, and U2OS (IC50 values ranging from 0.058 to 84.380 μM). Equisetin (8) showed bactericidal activities against Bacillus cereus and Listeria monocytogenes (MBC values of 7.8 and 31.25 µM, respectively), and bacteriostatic activity against Enterococcus faecalis (MIC value of 31.25 µM). Compounds 2 and 4 showed bacteriostatic activities against Listeria monocytogenes (MIC of 125 µM).

Keywords: Fusarium equiseti; antimicrobial activity; cytotoxicity; fusarochromanone; protein kinase inhibitors.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification
  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification
  • Antineoplastic Agents / pharmacology
  • Aquatic Organisms
  • Cell Line, Tumor
  • Chromones* / chemistry
  • Chromones* / isolation & purification
  • Chromones* / pharmacology
  • Fusarium* / drug effects
  • Humans
  • Microbial Sensitivity Tests
  • Protein Kinase Inhibitors / chemistry
  • Protein Kinase Inhibitors / isolation & purification
  • Protein Kinase Inhibitors / pharmacology

Substances

  • Chromones
  • Anti-Bacterial Agents
  • Antineoplastic Agents
  • Protein Kinase Inhibitors

Grants and funding

G.N. Pham has received funding from the European Union’s Horizon 2020 research and innovation program under the Marie Curie grant agreement N°847581 (COFUND BoostUrCAreer program), from the Région SUD Provence-Alpes-Côte d’Azur and IDEX UCAjedi. M. Dayras was the recipient of a thesis grant from the “Conseil Regional Provence-Alpes-Côte d’Azur”. S. Bach was supported by the French ANR/Investissements d’Avenir program via the OCEANOMICs project (grant #ANR-11-BTBR-0008). We thank the Canceropôle Provence-Alpes-Côte d’Azur and the Provence-Alpes-Côte d’Azur Region for the financial support provided to the MetaboCell and MetaboPure projects.